(1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate → P2,P3 Ketoamide derivative

HRID 1180759Notes

Reaction equation

[CH3:1][N:2]([CH3:41])[S:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:24][C:25](=[O:40])[O:26][CH2:27][C:28]1([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH2:31][CH2:30][CH2:29]1)[CH:12]([OH:23])[C:13](=[O:22])[NH:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:5])=[O:4].OC([C@@H](NC(=O)OCC1(CC2C=CC=CC=2)CCCCC1)CCCCNC(N1CCOCC1)=O)C(=O)N[C@@H](C1C=CC=CC=1)C>>[CH3:41][N:2]([CH3:1])[S:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:24][C:25](=[O:40])[O:26][CH2:27][C:28]1([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[CH2:31][CH2:30][CH2:29]1)[C:12](=[O:23])[C:13](=[O:22])[NH:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:4])=[O:5]

Participants

Reactant 2

HCID 58979648(1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate

HCID 58979653[1-(4-fluorobenzyl)cyclobutyl]methyl(1S)-5-{[(dimethylamino)sulfonyl]amino}-1-{1-hydroxy-2-oxo-2-[(3-pyridinylmethyl)amino]ethyl}pentylcarbamate

Product 1

HCID 10129151P2,P3 Ketoamide derivative

Procedure

[1-(4-Fluorobenzyl)cyclobutyl]methyl(1S)-5-{[(dimethylamino)sulfonyl]amino}-1-{oxo[(3-pyridinylmethyl)amino]acetyl}pentylcarbamate was prepared as in example 9j except that [1-(4-fluorobenzyl)cyclobutyl]methyl(1S)-5-{[(dimethylamino)sulfonyl]amino}-1-{1-hydroxy-2-oxo-2-[(3-pyridinylmethyl)amino]ethyl}pentylcarbamate was substituted for (1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate. 1H NMR (300 MHz, 80° C., DMSO-d6) δ 9.07 (m, 1H), 8.52 (s, 1H), 8.47 (d, J=5 Hz, 1H), 7.68 (d, J=8 Hz, 1H), 7.33 (m, 1H), 7.21 (m, 2H), 7.08 (t, J=9 Hz, 2H), 6.82 (m, 1H), 4.85 (m, 1H), 4.40 (d, J=6 Hz, 2H), 3.81 (s, 2H), 3.10 under water peak (m, 2H), 2.92 (m, 2H), 2.70 (s, 6H), 1.70-1.95 (m, 6H), 1.37-1.65 (m, 6H). ES-LCMS m/z 592 (M+H).

Sources & evidence

ORD record: ord-8532293bfffb41448e7807d6a3a3983a
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282512B2

Reaction notes

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